GB1083409A - Heterocyclic phosphorus-containing compounds - Google Patents
Heterocyclic phosphorus-containing compoundsInfo
- Publication number
- GB1083409A GB1083409A GB27720/65A GB2772065A GB1083409A GB 1083409 A GB1083409 A GB 1083409A GB 27720/65 A GB27720/65 A GB 27720/65A GB 2772065 A GB2772065 A GB 2772065A GB 1083409 A GB1083409 A GB 1083409A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- radical containing
- hydrocarbyl radical
- formula
- attached
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title abstract 6
- 125000000623 heterocyclic group Chemical group 0.000 title abstract 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title 1
- 229910052698 phosphorus Inorganic materials 0.000 title 1
- 239000011574 phosphorus Substances 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 12
- 239000000654 additive Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 239000000463 material Substances 0.000 abstract 3
- -1 nitro- Chemical class 0.000 abstract 3
- 229920005830 Polyurethane Foam Polymers 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 239000006260 foam Substances 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 239000004814 polyurethane Substances 0.000 abstract 2
- 229920002635 polyurethane Polymers 0.000 abstract 2
- 239000011496 polyurethane foam Substances 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- 230000000996 additive effect Effects 0.000 abstract 1
- 239000002671 adjuvant Substances 0.000 abstract 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- 239000003063 flame retardant Substances 0.000 abstract 1
- 150000008282 halocarbons Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 239000005056 polyisocyanate Substances 0.000 abstract 1
- 229920001228 polyisocyanate Polymers 0.000 abstract 1
- 229920005862 polyol Polymers 0.000 abstract 1
- 150000003077 polyols Chemical class 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 230000006641 stabilisation Effects 0.000 abstract 1
- 238000011105 stabilization Methods 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 1
- 125000005270 trialkylamine group Chemical group 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/5399—Phosphorus bound to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
- C07F9/65842—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
- C07F9/65848—Cyclic amide derivatives of acids of phosphorus, in which two nitrogen atoms belong to the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3878—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus
- C08G18/3889—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus having nitrogen in addition to phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
A polymeric material contains as additive a compound of the formula <FORM:1083409/C3/1> wherein CnH2n represents an alkylene group containing from 1 to 12 carbon atoms, at least one and not more than three adjacent carbon atoms in the alkylene radical forming a chain one end of which is attached to Y and the other end of which is attached to N, thereby completing the heterocyclic ring; R1 is a hydrocarbenyl radical containing from 1 to 18 carbon atoms or a halo-, nitro-, C1- 8-alkoxy-, C1- 8-alkyl-mercapto- or cyano-substituted hydrocarbyl radical containing from 1 to 18 carbon atoms; R11 is hydrogen, a hydrocarbyl radical containing from 1 to 18 carbon atoms or the radical -CONHR111, wherein R111 represents a hydrocarbyl radical containing from 1 to 18 carbon atoms; and Y is -O- or -NR11- wherein R11 has the significance defined above and wherein R11 may be the same as or different from R11 in the group -NR11-. The additives may be used to improve the fire-retarding properties of polyurethane foams by adding them to the mixes used in the production of such foams or, in the cases of those compounds in which R11 is hydrogen and Y is -NH-, by incorporating them into the polyurethanes by adding them to the reaction mixture of polyisocyanate and polyol from which the polyurethanes are prepared. Also, the additives are useful for the stabilization of polymeric materials, e.g. polyvinyl chloride and copolymers thereof, towards ultra-violet radiation. For this purpose they may be blended into the mixture containing the polyvinyl compounds, plasticizer and other conventional adjuvants.ALSO:Novel compounds of the formula <FORM:1083409/C2/1> wherein CnH2n is an alkylene group containing from 1 to 12 carbon atoms, at least one and not more than 3 adjacent carbon atoms in the alkylene radical forming a chain one end of which is attached to Y and the other end of which is attached to N thereby completing the heterocyclic ring; R1 is a hydrocarbyl radical containing from 1 to 18 carbon atoms or a halo-, nitro-, C1- 8-alkoxy-, C1- 8-alkylmercapto- or cyano-substituted hydrocarbyl containing from 1 to 18 carbon atoms; R11 is hydrogen, a hydrocarbyl radical containing from 1 to 18 carbon atoms or the radical -CONHR111 wherein R111 represents a hydrocarbyl radical containing from 1 to 18 carbon atoms; and Y is -O- or -NR11- wherein R11 has the significance defined above and wherein R11 may be the same or different from R11 in the group -NR11-, are prepared by reacting diamines or alkanol amines of the formula HYCnH2nNHR11 with phosphonic dihalides of the formula R1POHal2, wherein Hal represent s halogen, in the presence of an acid accept t and an inert organic solvent at reaction temperatures up to 100 DEG C. The said acceptor may be a tertiary amine, e.g. pyridine, a tri-alkylamine, an N-alkyl piperidine, an N-alkylmorpholine or an N-dialkylaniline, or an inorganic base, e.g. an alkali-metal carbonate or hydroxide, and specified inert solvents are hydrocarbons and halogenated hydrocarbons. The compounds are useful as fire retardants, e.g. by addition to foam mixers used in the production of polyurethane foams (see Division C3), and as stabilizers of polymeric materials (see Division C3).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38919364A | 1964-08-12 | 1964-08-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1083409A true GB1083409A (en) | 1967-09-13 |
Family
ID=23537239
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB37275/66A Expired GB1083410A (en) | 1964-08-12 | 1965-06-30 | Novel process for the preparation of carbodiimides, and certain carbodiimides so produced |
| GB27720/65A Expired GB1083409A (en) | 1964-08-12 | 1965-06-30 | Heterocyclic phosphorus-containing compounds |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB37275/66A Expired GB1083410A (en) | 1964-08-12 | 1965-06-30 | Novel process for the preparation of carbodiimides, and certain carbodiimides so produced |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3522303A (en) |
| DE (1) | DE1620609C3 (en) |
| GB (2) | GB1083410A (en) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3943153A (en) * | 1968-09-06 | 1976-03-09 | Merck & Co., Inc. | (-)(Cis-1,2-epoxy propyl)phosphonic acid amides |
| BE787395A (en) * | 1971-08-13 | 1973-02-12 | Basf Wyandotte Corp | POLYISOCYANATES PREPARATION PROCESS |
| US3957923A (en) * | 1973-06-25 | 1976-05-18 | E. I. Du Pont De Nemours & Company | Alkyl and haloalkyl n,n'-dialkyl-n-methylolphosphorodiamidates |
| US3980618A (en) * | 1973-08-06 | 1976-09-14 | Monsanto Company | Cyclic organophosphorus amides |
| US3911005A (en) * | 1974-09-12 | 1975-10-07 | Monsanto Co | 1,3,2-Diazaphospholidine compounds |
| DE2504400A1 (en) | 1975-02-01 | 1976-08-05 | Bayer Ag | STORAGE-STABLE POLYISOCYANATE CONTAINING CARBODIIMIDE GROUPS |
| US4166071A (en) * | 1977-12-28 | 1979-08-28 | The United States Of America As Represented By The Secretary Of The Air Force | Monophospha-s-triazines |
| DE4238046A1 (en) * | 1992-11-11 | 1994-05-19 | Basf Ag | New bis (4-substituted-2,6-diisopropylphenyl) carbodiimides, a process for their preparation and their use and the 4-substituted 2,6-diisopropylphenyl isocyanates which can be used for their preparation |
| US6184410B1 (en) | 1998-05-14 | 2001-02-06 | Basf Aktiengesellschaft | Carbodiimides based on 1,3-bis(1-methyl-1-isocyanatoethyl)benzene |
| DE10000656A1 (en) | 2000-01-11 | 2001-07-12 | Basf Ag | New compatible hydrophilic compounds containing carbodiimide units and carboxyl or carboxylate groups are useful in increasing the molecular weight of aqueous polymer dispersions for use as adhesives or coatings |
| US8076445B2 (en) | 2000-01-11 | 2011-12-13 | Robert Shane Porzio | Oligocarbodiimides for the formation of crosslinked latex films |
| DE10015658A1 (en) * | 2000-03-29 | 2001-10-04 | Rhein Chemie Rheinau Gmbh | Block copolymers based on polycarbodiimides, a process for their preparation and their use as hydrolysis stabilizers |
| WO2009112467A1 (en) | 2008-03-11 | 2009-09-17 | Basf Se | Microcapsules with acylurea walls |
| EP2350228A1 (en) | 2008-10-29 | 2011-08-03 | Basf Se | A proppant |
| US9714378B2 (en) | 2008-10-29 | 2017-07-25 | Basf Se | Proppant |
| WO2012104190A1 (en) | 2011-01-31 | 2012-08-09 | Basf Se | A proppant |
| ES2758029T3 (en) | 2011-08-30 | 2020-05-04 | Basf Se | High molecular weight polycarbodiimide and its production method |
| US8778456B2 (en) | 2011-08-30 | 2014-07-15 | Basf Se | Coating composition including high molecular weight polycarbodiimide, method of preparing same, and method of preparing coating on a substrate |
| EP2660259A1 (en) * | 2012-05-03 | 2013-11-06 | Rhein Chemie Rheinau GmbH | New compositions containing carbodiimide, method for their production and use |
| WO2015123416A1 (en) | 2014-02-14 | 2015-08-20 | Basf Se | Method of preparing a polycarbodiimide polymer and polycarbodiimide polymer prepared thereby |
| KR20160124804A (en) | 2014-02-20 | 2016-10-28 | 바스프 에스이 | Post-modified polycarbodiimides |
| US10435499B2 (en) | 2015-02-03 | 2019-10-08 | Basf Se | Solvent-borne system for forming an n-acyl urea coating |
| JP2018517073A (en) | 2015-05-18 | 2018-06-28 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | Paperboard and paper media processing method and related processed paperboard and paper media |
| JP2018528296A (en) * | 2015-07-31 | 2018-09-27 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | Colored primer composition for forming an N-acyl urea coating agent |
| RU2019127966A (en) | 2017-02-06 | 2021-03-09 | Басф Се | WATER SYSTEM FOR COATING ON SUBSTRATE |
| EP3945110A1 (en) | 2020-07-30 | 2022-02-02 | Clariant International Ltd | Flame retardant stabilizer combinations for flame-resistant polymers having improved resistance to hydrolysis and their use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1065418B (en) * | 1953-03-21 | 1959-09-17 | Montecatini Soc. Gen. per 1'Industria Mineraria e Chimica, Mailand (Italien) | Process for the preparation of heterocyclic phosphorus compounds |
| US3285999A (en) * | 1963-06-07 | 1966-11-15 | Continental Oil Co | Thioamidophospholanes |
-
1964
- 1964-08-12 US US389193A patent/US3522303A/en not_active Expired - Lifetime
-
1965
- 1965-06-30 GB GB37275/66A patent/GB1083410A/en not_active Expired
- 1965-06-30 GB GB27720/65A patent/GB1083409A/en not_active Expired
- 1965-08-11 DE DE1620609A patent/DE1620609C3/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1620609A1 (en) | 1970-04-30 |
| US3522303A (en) | 1970-07-28 |
| DE1620609C3 (en) | 1973-10-04 |
| DE1620609B2 (en) | 1973-03-08 |
| GB1083410A (en) | 1967-09-13 |
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